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Structure of Amines

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are...

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Cationic Nitrogen-Doped Helical Nanographenes.

Kun Xu¹, Yubin Fu¹, Youjia Zhou¹

¹Center for Advancing Electronics Dresden (cfaed), Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062, Dresden, Germany.

Angewandte Chemie (International Ed. in English)

|September 14, 2017

Summary

This summary is machine-generated.

Researchers developed new chiral, nonplanar cationic nitrogen-doped nanographenes (CNDNs). These CNDNs exhibit lower energy gaps and unique electronic properties, opening new avenues for advanced graphene materials.

Keywords:

graphene helicene nanographene nitrogen doping polycyclic aromatic hydrocarbons

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Area of Science:

Organic Chemistry
Materials Science
Nanotechnology

Background:

Nanographenes are carbon-based nanomaterials with unique electronic and optical properties.
Introducing heteroatoms like nitrogen can tune these properties for specific applications.
Achieving controlled chirality and nonplanar geometries in nanographenes remains a synthetic challenge.

Purpose of the Study:

To design and synthesize novel cationic nitrogen-doped nanographenes (CNDNs) with nonplanar geometry and axial chirality.
To investigate the electronic and optical properties of these CNDNs and compare them to all-carbon analogues.
To explore the electrochemical behavior and reduction products of CNDNs.

Main Methods:

Synthesis of cationic nitrogen-doped nanographenes.
Single-crystal X-ray diffraction for structural analysis.
Spectroscopic techniques (UV-Vis, electrochemistry) to determine electronic and optical properties.
In situ spectroelectrochemical studies to probe reduction mechanisms.

Main Results:

Successful synthesis of CNDNs with helical and cove-edged structures confirmed by X-ray analysis.
CNDNs exhibit lower-lying frontier orbitals, reduced optical energy gaps, and enhanced electron-accepting capabilities compared to all-carbon counterparts.
Cyclic voltammetry revealed quasireversible reductions.
Spectroelectrochemical studies demonstrated the formation of neutral radicals or radical cations upon reduction, dependent on nitrogen dopant concentration.

Conclusions:

The study successfully introduced cationic nitrogen doping and axial chirality into nanographenes.
These novel CNDNs possess tunable electronic properties and unique structural features.
The findings provide a foundation for designing advanced graphene materials, including expanded nanographenes and graphene nanoribbons with tailored properties.